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Silylation of Pyridine, Picolines, and Quinoline with a Zinc Catalyst.

ABSTRACT: Zn(OTf)2 (OTf- = trifluoromethanesulfonate) catalyzes the silylation of pyridine, 3-picoline, and quinoline to afford the silylated products, where the silyl groups are meta to the nitrogen. The isolated yields of the products range from 41 to 26%. The 2- and 4-picolines yielded the silylmethylpyridines, where the CH3 groups were silylated instead of the ring. The pyridine silylation can occur via two separate pathways, involving either a 1,4- or a 1,2-hydrosilylation of pyridine as the first step. A byproduct of the pyridine silylation is a head-to-tail dimerization of N-silyl-1,4-dihydropyridine to form a diazaditwistane molecule.

SUBMITTER: Prybil JW

PROVIDER: S-EPMC6990635 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Silylation of Pyridine, Picolines, and Quinoline with a Zinc Catalyst.

Prybil Joshua W JW Wallace Rodney R Warren Alexandra A Klingman Jordan J Vaillant Romane R Hall Michael B MB Yang Xin X Brennessel William W WW Chin Robert M RM

ACS omega 20200110 3

Zn(OTf)2 (OTf- = trifluoromethanesulfonate) catalyzes the silylation of pyridine, 3-picoline, and quinoline to afford the silylated products, where the silyl groups are meta to the nitrogen. The isolated yields of the products range from 41 to 26%. The 2- and 4-picolines yielded the silylmethylpyridines, where the CH3 groups were silylated instead of the ring. The pyridine silylation can occur via two separate pathways, involving either a 1,4- or a 1,2-hyd ...[more]

PMID: 32010826

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